US1853435A - Substituted sulphur dyestuff - Google Patents
Substituted sulphur dyestuff Download PDFInfo
- Publication number
- US1853435A US1853435A US460093A US46009330A US1853435A US 1853435 A US1853435 A US 1853435A US 460093 A US460093 A US 460093A US 46009330 A US46009330 A US 46009330A US 1853435 A US1853435 A US 1853435A
- Authority
- US
- United States
- Prior art keywords
- sulphur
- group
- prepared
- sulphurating
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 15
- 239000005864 Sulphur Substances 0.000 title description 13
- 239000000975 dye Substances 0.000 title description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- 239000000835 fiber Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000004043 dyeing Methods 0.000 description 7
- 235000013311 vegetables Nutrition 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 2
- 150000003945 chlorohydrins Chemical class 0.000 description 2
- AMDQVKPUZIXQFC-UHFFFAOYSA-N dinaphthylene dioxide Chemical compound O1C(C2=C34)=CC=CC2=CC=C3OC2=CC=CC3=CC=C1C4=C32 AMDQVKPUZIXQFC-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QLRKASHXFNIPLZ-UHFFFAOYSA-M benzyl-dimethyl-phenylazanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[N+](C)(C)CC1=CC=CC=C1 QLRKASHXFNIPLZ-UHFFFAOYSA-M 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YCYOWIYHCRGAAH-UHFFFAOYSA-M trimethyl(naphthalen-1-yl)azanium;chloride Chemical compound [Cl-].C1=CC=C2C([N+](C)(C)C)=CC=CC2=C1 YCYOWIYHCRGAAH-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/30—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using sulfur dyes
Definitions
- Patented Apr. 12, 1932 stirs ERWIN KRAMER, CF GOLOGNE-DEU'IZ, AND BERNABD BOLLWEG AND LUDWIG. ZEZE1'.,, OF LEVERKUSEN-ON-THE-RHINE, GERMANY, ASSIGNORS 7130, GENERAL .AN'IILLNJ'E.
- the present invention relates to a process of preparing substituted sulphur dyestuffs on the fiber and to the fibers dyed with said substituted sulphur dyestuffs.
- Ewampe 1 The dyeing obtained on cotton by means of the sulphur dyestufl produced by heating tetrachlorodinaph'thylenedioxide with sodium sulphide according to the direction of British specification 325,519, Example 3, is squeezed and rinsed and then drawn for 10-20 minutes through a boiling bath, which is charged with 2-t cm. of caustic soda lye (40 B.), 1,5 grams of hydrosulphite and 10 grams of dimethylbene zylphenylammonium chloride to the liter. A. very clear, reddish orange dyeing is ob tained. Trimethylnaphthylammonium chloride yields a more yellowish: shade, whilethe, chlorohy-drins yield brick red shades.
- Example 2 By using the sulphur dyestuif which is obtainedfrom pentachlorodinaphthylenedioxide by heating with sulphur and sodium sulphide-as is described in British specification 325,519,, Example 4, and employing dimethylbenzylphenylammonium chlo ride a clear, strongly yellowish red is ob tained, while the chlorohydrins yield red shades.
- the process which comprises dyeing vegetable fibers with a sulphur dyestuff prepared by sulphurating a compound of the group consisting of tetrachlorodinaphthyl- I enedioxide and pentachlorodinaphthyienedioxide, rinsing same and boiling them in an equ-eous bath containing a small amount of alkali, a reducing agent and a compound of the group consisting of alkylating, aralkylating and arylating agents.
- a benzylated sulphur dyestufi' prepared by sulphurating a compound of the. group consisting of tetrachlorodinaphthylenedioxide and pentachlorodinaphthylenedioxide
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
Patented Apr. 12, 1932 stirs ERWIN KRAMER, CF GOLOGNE-DEU'IZ, AND BERNABD BOLLWEG AND LUDWIG. ZEZE1'.,, OF LEVERKUSEN-ON-THE-RHINE, GERMANY, ASSIGNORS 7130, GENERAL .AN'IILLNJ'E.
WQRKS, INQ, OF NEW YORK, N. Y., A
COIEt-PORAEION OF DELAWARE SUBSTITUTED snLrnun nYEsrUrr No Drawing. Application filed June 9, 1930, Serial No. 160,093, and in Germany .Tune 13, 19292- I The present invention relates to a process of preparing substituted sulphur dyestuffs on the fiber and to the fibers dyed with said substituted sulphur dyestuffs.
5' In the process hereinafter described we use as starting materials the sulphur dyestuffs which are obtainable by reacting upon a halogenerated dinaphthylenedioxide with a sulphurating agent at elevated temperatures which process is more fully described in the British specification 325,519.
lVe have found that new valuable substituted sulphur dyestuffs canbe prepared on vegetable fibers by dyeing in the usual manner the fibers with one of the above men tioned sulphur dyestuffs, rinsing the goods and treating them with a solution of an a1- rylating, aralkylating or arylating agent, for instance, with a solution of dimethyl-benzylphenyl-ainmonium chloride at an elevated temperature, favorably in a boiling bath and preferably in the presence of an agent capable of exerting a reducing action and of a small amount of alkali, said process being described in U. S. Letters Fatent 688,999.
By working at alower temperature or without the addition of a reducing agent, the development is retarded and it may, according to the agents used, in the subsequent treatment entirely fail to take place. The dyeings obtained display very satisfactory fastness to boiling, and kier boiling. The shades obtainable according to our new process are yellow, orange and red.
The invention is illustrated by the following examples, without being limited thereto:
Ewampe 1.The dyeing obtained on cotton by means of the sulphur dyestufl produced by heating tetrachlorodinaph'thylenedioxide with sodium sulphide according to the direction of British specification 325,519, Example 3, is squeezed and rinsed and then drawn for 10-20 minutes through a boiling bath, which is charged with 2-t cm. of caustic soda lye (40 B.), 1,5 grams of hydrosulphite and 10 grams of dimethylbene zylphenylammonium chloride to the liter. A. very clear, reddish orange dyeing is ob tained. Trimethylnaphthylammonium chloride yields a more yellowish: shade, whilethe, chlorohy-drins yield brick red shades.
Example 2.By using the sulphur dyestuif which is obtainedfrom pentachlorodinaphthylenedioxide by heating with sulphur and sodium sulphide-as is described in British specification 325,519,, Example 4, and employing dimethylbenzylphenylammonium chlo ride a clear, strongly yellowish red is ob tained, while the chlorohydrins yield red shades.
Furthermore by subsequent treatment with the dyestuff prepared from tetrabromodinaphthylenedioxide according to Example 5 of the British specification 825,519, yellow shades are produced, while the dyestuif prepared from hexachlorodinaphthylenedioxide according to Example 6 of British specification 325,519 leads to strongly bluish-red shades.
e claim:
1. The process which comprises dyeing vegetable fibers with a sulphur dyestufl prepared by sulphurating a halogenated dinaph- 'thylenedioxide, rinsing same and boiling them m an aqueous bath containing a small amount of alkali, a reducing agent and a compound of the group consisting of alkylating aralkylating and arylating agents.
2. The process which comprises dyeing vegetable fibers with a sulphur dyestuff prepared by sulphurating a compound of the group consisting of tetrachlorodinaphthyl- I enedioxide and pentachlorodinaphthyienedioxide, rinsing same and boiling them in an equ-eous bath containing a small amount of alkali, a reducing agent and a compound of the group consisting of alkylating, aralkylating and arylating agents.
3. The process which comprises dyeing vegetable fibers with a sulphur dyestuif prepared by sulphurating a compound of the group consisting of tetrachlorodinaphthylenedioxide and pentachlorodinaphthylenedioxide, rinsing same and drawing them through a boiling bath which is chared with 2 1 cm. of caustic soda lye (40 B), 1.5 grams of hydrosulfite and 10 grams of di-. Inethylbenzylphenylammonium chloride to the liter.
4. Vegetable fibers dyed with a dyestufi of the group consisting of a1ky1ated,vara1ky1-V ated and arylated sulphur dyestufi'sprepared by sulphurating a, halogenated dinaphthylenedioxide. I
5. Vegetable fibers dyed with a dyestufi of the group consisting of alkylated, aralkylated and arylated sulphur dyestuffs prepared by sulphurating a compound of the group 10 consisting of tetrachlorodinaphthylenedioxide and pentachlorodinaphthylenedioxide.
6. Vegetable fibers dyed with a benzylated sulphur dyestufi' prepared by sulphurating a compound of the. group consisting of tetrachlorodinaphthylenedioxide and pentachlorodinaphthylenedioxide In testimony whereof, we afiix our signatures. 7 V ERWIN KRAMER.
- BERNHARD BOLLWEG.
LUDWIG ZEH.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1853435X | 1929-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1853435A true US1853435A (en) | 1932-04-12 |
Family
ID=7746102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US460093A Expired - Lifetime US1853435A (en) | 1929-06-13 | 1930-06-09 | Substituted sulphur dyestuff |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1853435A (en) |
-
1930
- 1930-06-09 US US460093A patent/US1853435A/en not_active Expired - Lifetime
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